Winston Churchill's tailors told us he owed them so much money they sent a bill to Downing Street on his first day as Prime Minister -- and it didn't go down well

Savile Rowe tailors Henry Poole & Co were tasked with dressing Gary Oldman for his role as Winston Churchill in Oscar-nominated film “Darkest Hour.”

The tailors dressed the real Churchill throughout his life.

They describe him as a “character,” who owed money and ‘was always having to be looked after.’

Henry Poole & Co., one of the oldest tailors on London’s Savile Row, was given just seven weeks to create the suits worn by Gary Oldman in this year’s Oscar-nominated film “Darkest Hour,” in which Oldman plays former Prime Minister Winston Churchill.

“Normally we’re looking at around 12 weeks to do any kind, of suit, so this was a challenge,” Poole’s managing director, Simon Cundey, told Business Insider.

But if anyone could do it, it’s a company that knows Churchill’s style inside and out. The tailor, established in 1806, dressed the former PM himself from the age of 35.

“His father, Lord Randolph Churchill, was here as a customer and he had suits made,” Cundey said. While Randolph died at a young age, Winston came to Poole in 1905, according to Cundey, and he ordered his first uniform in 1906 – the Trinity Uniform.

You can see his orders in the book below:

Henry Poole & Co

Cundey’s great-grandfather Howard Cundey initially looked after Churchill, while his grandfather Sam Cundey saw him through his later years.

“We saw him evolve into what was a great Prime Minister, [but] we took him as a young junior with his slim build at the time,” Cundey said.

“He had quite a small body for a big head in some respects. We were actually making his shoulders a bit wider, making a bit more chest on him, but of course that all changed later as he changed his shape.”

He added that in his prime, Churchill was a “dandy dresser.”

According to Cundey, over the years – particularly in his 20s – Churchill was “roaring with his clothing in his wardrobes, ordering absolutely everything from suits to uniforms.”

“The only thing we didn’t make was his siren suit, which of course he’s known for as well.”

The most iconic Churchill look from Poole by far was his Chalk Stripe flannel, which he’s wearing in his famous 1936 Tommy gun photo, shown below.

Cundey even had the image on his teacup when we met.

Henry Poole & Co

The company still works with the mills that made that cloth, though it’s been made to be a bit lighter – back then it was made with “bulletproof, heavy fabric.”

Here’s what it looks like today:

Henry Poole & Co

A bit like ‘The Devil Wears Prada’

Despite his appeal, working with Churchill was far from easy.

“He was always having to be looked after,” Cundey said. “A bit like ‘The Devil Wears Prada,’ he would throw the coat and pass it to somebody. He was that sort of character.”

He added: “My grandfather, as much as I know, always had to check the pockets for stubbed cigars in the side pockets – they always were there.”

Cundey also said Churchill “wasn’t the greatest payer.”

“He was a slower payer, shall we say,” he said. “There was a point where he did owe quite a bit of money.”

He said the company’s chief accountant “instead of being diplomatic with his ways of asking for payment… thought it would be upper hand and [get] a quicker response to send [the bill] to Downing Street on the day that he was made Prime Minister.

“So we did, and whilst poor Winston was getting ‘congratulations on your new position,’ our bill came in and it did not go down too well as you can imagine.”

The company received a letter saying “Thank you for your services,” but luckily they later made up.

“He came back and we made him more,” Cundey said. “We did a lot of little repairs and things, especially for the coronation for Queen Elizabeth. He really wanted to make a big effort for that.”

Turning Gary Oldman into Churchill

Despite his quirks, Cundey said Churchill was a “very elegant” and “forward-thinking man,” or so he was told by his grandfather – and it was this admiration of his character that led the company to work on “Darkest Hour.”

“It’s not often that Poole does films,” Cundey said – they turned down working with the Kingsman franchise because they didn’t want the name in their window. However, he added: “How could you turn down the Prime Minister, or working with him?”

They were approached by Oscar-winning costumer designer Jacqueline Durran – known for “Beauty and the Beast” and “Anna Karenina” – and thought “this must be someone of high calibre,” Cundey said.

Jack English / Focus Features

“When she mentioned [Director] Joe Wright, who gave you ‘Pride and Prejudice’ and ‘Atonement’ and all those great films, we thought, ‘This is really going to be a good-quality piece.'”

However, with Oldman based in Los Angeles, putting the suits together was almost as difficult as working with Churchill himself.

“The prosthetic body suit [he wore under his clothes] was being made for him in Hollywood, so a Japanese gentleman was measuring him out there for the costume,” Cundey said. “We had to go out there to measure him with the [prosthetic] suit on, and then go back and measure him for the first fitting when he was coming over to do his first rehearsals.

“We did it, came back, got the pattern ready, got the cloth ready,” he said.

Jack English / Focus Features

Luckily, it was all worth it – and the film’s six Oscar nominations include one for Best Achievement in Costume Design for Durran.

“Instantly, as soon as he put a waistcoat and trousers on, Gary was off,” Cundey said. “He was into his role of playing Churchill, and the mannerisms came in. He was walking up and down holding his lapels… that kind of motion was very much how Churchill was when he spoke to you.”

Two of the suits worn by Oldman in the film now sit in Poole’s show window…

Henry Poole & Co

…alongside the Churchill shoes…

Alison Millington

…and Homburg hat.

Alison Millington

The company, known for dressing Her Majesty the Queen in her ceremonial cloaks, also dressed Ben Mendelsohn, who played King George VI (the Queen’s father), shown in the image below.

Jack English / Focus Features

“To do his naval uniform was an enjoyment too,” he said. “This was a warrant we were granted back with Queen Victoria in the day and latterly done with Queen Elizabeth. We’re very proud of the fact we do that today.”

And it wasn’t just Poole the film got on board – according to Cundey, they went to all of the tailors that worked with Churchill.

“There’s a great little Churchill walk you can now do, of all the houses he frequented here in Mayfair and St. James’s,” he said.

“Sadly, poor old Gary didn’t get a chance to have the suit at the end of the day, because they didn’t really fit him,” he joked. Due to the prosthetic body suit, the cuts were far too big for him.

However, he added: “Ben got himself a lovely Savile Row suit from Henry Poole, so he was a lucky man.”